(E)-4-Chloro-N-[4-(methyl­sulfon­yl)benzyl­idene]aniline

Chen, Y.-H.; Wang, F.; Li, G.-Q.; Qian, S.-S.

doi:10.1107/S160053681105361X

Volume 68
Part 1
Page o166
January 2012

Received 26 November 2011
Accepted 13 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.038
wR = 0.110
Data-to-parameter ratio = 19.2
Details

(E)-4-Chloro-N-[4-(methylsulfonyl)benzylidene]aniline

Yue-Hu Chen,^a Fang Wang,^a Guo-Qiang Li ^a and Shao-Song Qian ^a ^*

^aSchool of Life Sciences, ShanDong University of Technology, ZiBo 255049, People's Republic of China
Correspondence e-mail: njuqss@yahoo.com.cn

In the crystal structure of the title compound, C₁₄H₁₂ClNO₂S, the molecules display a trans conformation with respect to the C=N double bond. The dihedral angle between the methylsulfonyl benzene and chlorobenzene rings is 59.59 (8)°. The crystal packing is stabilized by weak C-HO interactions and by [pi] - [pi] stacking interactions between inversion-related methylsulfonyl benzene rings [centroid-centroid distance = 3.8579 (11) Å].

Related literature

For background to the pharmacological properties of Schiff base compounds, see: Villar et al. (2004); Pandey et al. (1999); Singh & Dash (1988). For related structures, see: Qian & Cui (2009); Qian & Liu (2010).

Experimental

Crystal data

C₁₄H₁₂ClNO₂S
M_r = 293.77
Monoclinic, P 2₁ /n
a = 8.6206 (10) Å
b = 8.8748 (10) Å
c = 17.799 (2) Å
= 94.972 (1)°
V = 1356.6 (3) Å³
Z = 4
Mo K radiation
= 0.43 mm^-1
T = 296 K
0.25 × 0.23 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.898, T_max = 0.913
11492 measured reflections
3320 independent reflections
2596 reflections with I > 2(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.110
S = 1.04
3320 reflections
173 parameters
H-atom parameters constrained
_max = 0.29 e Å^-3
_min = -0.40 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7O1ⁱ	0.93	2.56	3.126 (2)	120
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2372 ).

Acknowledgements

This project was sponsored by the ShanDong Province Science & Technology Innovation Foundation (People's Republic of China).

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Pandey, S. N., Sriram, D., Nath, G. & De Clercq, E. (1999). Farmaco, 54, 624-628.
Qian, S.-S. & Cui, H.-Y. (2009). Acta Cryst. E65, o3093.
Qian, S.-S. & Liu, T. (2010). Acta Cryst. E66, o18.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Singh, W. M. & Dash, B. C. (1988). Pesticides, 22, 33-37.
Villar, R., Encio, I., Migliaccio, M., Gil, M. J. & Martinez-Merino, V. (2004). Bioorg. Med. Chem. 12, 963-968.

organic compounds